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Synlett 2014; 25(07): 932-934
DOI: 10.1055/s-0033-1340919
letter
© Georg Thieme Verlag Stuttgart · New York

Improved Conditions for the Proline-Catalyzed Aldol Reaction of Acetone with Aliphatic Aldehydes

Alberto Martínez
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany   Fax: +49(208)3062999   eMail: list@mpi-muelheim.mpg.de
,
Kristina Zumbansen
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany   Fax: +49(208)3062999   eMail: list@mpi-muelheim.mpg.de
,
Arno Döhring
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany   Fax: +49(208)3062999   eMail: list@mpi-muelheim.mpg.de
,
Manuel van Gemmeren
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany   Fax: +49(208)3062999   eMail: list@mpi-muelheim.mpg.de
,
Benjamin List*
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany   Fax: +49(208)3062999   eMail: list@mpi-muelheim.mpg.de
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Publikationsverlauf

Received: 04. Februar 2014

Accepted: 16. Februar 2014

Publikationsdatum:
25. März 2014 (online)

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Dedicated to Max Malacria on the occasion of his 65th birthday

Abstract

The proline-catalyzed asymmetric aldol reaction between aliphatic aldehydes and acetone has, to date, remained underdeveloped. Challenges in controlling this reaction include avoiding undesired side reactions such as aldol condensation and self-aldolization. In recent years we have developed optimized conditions, which enable high yields and good to excellent enantioselectivities, and which are presented in this communication.

Key words

aldehydes - aldol reaction - asymmetric catalysis - organocatalysis - proline

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

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